Diethyl Ether → HCID 11142708, compound

HRID 371300Notes

Reaction equation

HRID 371300 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])[C:7]2=[O:12].[CH2:26](OCC)C.[N+](=C)=[N-]>CO>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([O:17][CH3:26])=[O:16])[C:7]2=[O:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 156388WS-5995 B

Product 1

HCID 11142708HCID 11142708, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (50 ml) was dissolved 2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid (1 g) as obtained in Example 15, followed by addition of a diethyl ether solution of diazomethane (20 ml). The mixture was allowed to stand at room temperature for an hour, after which the diethyl ether and methanol were distilled off. The residue was subjected to silical gel chromatography and recrystallized from diethyl ether-n-hexane. The procedure yielded yellow crystals (500 mg) of methyl 2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate.

Workup

  1. customas obtained in Example 15
  2. waitto stand at room temperature for an hour
  3. distillationafter which the diethyl ether and methanol were distilled off
  4. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-c5399a7439b14727b35cb7587e7e885e
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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